Demetri Karagas had arrived at a pleasant predicament: enough time for long lunches. He had finished his post-deal stretch at Thirty Madison and Remedy at the end of 2025. There was travel with his family. There was a chance to recharge. There was, at last, room in the day for something besides building a company. By October 2026, he was announcing another one. Leisure had received a fair hearing.
The new venture is Sentinel, founded with Steven Gutentag and Blake Yoder. Karagas described becoming restless to build again. His choice of companions gives the announcement its particular charm. Gutentag has been beside him through businesses, a pivot, an acquisition and the years at Thirty Madison. Yoder worked with them there. For Karagas, starting afresh can involve rather familiar company.
A friendship with a long working history
Karagas and Gutentag met during their first week at NYU Stern. The setting offered ample encouragement toward a career in finance. Their shared interest ran toward making things of their own. Both had tried business before college, and they began exchanging ideas while studying. Their partnership would outlast the campus setting that produced it.
Karagas studied finance and history, attending Stern from 2006 to 2010. Those subjects make an agreeable pairing for a future founder: one asks how the numbers work; the other offers plentiful examples of people being surprised. The record of his subsequent ventures supplies evidence of both. His earliest company would change direction. His later company would grow, acquire businesses and eventually become an acquisition itself.
He came to New York from Corpus Christi, Texas. Before university, his entrepreneurial experiments included buying and selling things and a surf company while he was still at school. A visit to New York helped settle where he wanted to study. The move placed him in the city where his partnership with Gutentag and much of his business career would take shape.
After graduation came paid work and continued attention to their own venture. Acceptance into the first Entrepreneurs Roundtable Accelerator cohort forced the issue: participation required a full-time commitment. They left their jobs. The accelerator could offer guidance, but it could not make the decision for them. At some point, the promising side project had to occupy the middle of the day.
The browser idea that became a cleaning business
Sitesimon, their early venture, was a browser-based content recommendation service. Its premise belonged to a particular moment in the social web: people were sharing where they went and what they liked; perhaps they would share their browsing, too. Karagas publicly explained a service that could track a clickstream while letting users control who saw it and exclude particular websites.
It was a substantial proposition. Browsing history could become a route to discovery among friends, with privacy controls shaping what appeared. The business depended on people finding that exchange useful enough to adopt. Karagas was already working on a recurring question in his career: how much easier could a familiar activity become when software reorganised the experience?
Eventually, the founders concluded that Sitesimon was not working for them. They still had money, but judged that they were the wrong team for that business. They took a different proposal to their colleagues and investors: Get Maid. The leap from browser recommendations to apartment cleaning was considerable. Their willingness to make it mattered more than a tidy account of the original plan.
Get Maid made a concrete promise. A customer in New York could book through an app or website and have a vetted cleaner at the door within two hours. Payment, tax, tip and supplies were bundled into the transaction. A person with a dirty apartment could appreciate the proposition without a presentation. Dust has never required much customer education.
The company launched in December 2012 and expanded into Queens and Brooklyn. Running it meant handling the distance between a clean interface and a clean room. Scheduling, service and execution had to agree. An app could make the booking look effortless; someone still had to arrive at the door and do the work.
Homejoy acquired Get Maid in May 2014, and Karagas and Gutentag joined its New York team. Adora Cheung, Homejoy’s co-founder, praised their work ethic and described founders who had handled customer service, marketing and operations themselves. Her account even included cleaning through a hurricane. The early résumé contained rather more household labour than the average finance graduate might have anticipated.
A brand grows into an organisation
Karagas later worked at Google as a program manager. He and Gutentag then co-founded Thirty Madison in 2017, with Keeps launching in January 2018. By then they had experience both creating a small company and working inside larger organisations. The next undertaking would require them to build an organisation large enough to develop several brands.
The scale changed visibly in June 2021. Thirty Madison announced a $140 million Series C, bringing its total funding at that point to $210 million and valuing the business above $1 billion. New and existing investors participated. The company also reported that its revenue had tripled in 2020. These were company figures, marking a particular stage in its development.
Series C financing. Total funding then stood at $210 million.
The figures are easy to fit into a sentence. The organisation required to justify them takes longer to assemble. Each new colleague introduces another relationship, another handover, another person who must understand what good work looks like. For founders accustomed to doing several jobs themselves, growth changes the daily task. Much more work must happen through other people.
Thirty Madison’s expansion included its 2022 combination with Nurx. Karagas’s career now involved the buyer’s side of transactions as well as the seller’s. A transaction can bring an established business into the organisation quickly. After the announcement, the teams still have to work together. The calendar recognises a closing date; colleagues need rather more than a date to become a functioning company.
In his later conversation with Sari Kaganoff, Karagas reflected on hiring at a pace of 20 to 30 people a week and on losing some of the discipline that had helped the first brand succeed. It is an unusually useful detail in a founder’s retrospective. A headcount announcement can sound decisive. The work of keeping that growing team coordinated continues after the announcement has disappeared.
The sale, and the end of his shift
On September 3, 2025, Remedy Meds announced a definitive agreement to acquire Thirty Madison. Karagas was identified as its CEO and co-founder. The announcement described an all-stock transaction valued just above $500 million, with closing expected in the fourth quarter. The distinction matters: this was the announced structure and timetable of the deal.
For Karagas, the transaction eventually brought a personal change of schedule. He has since said that his post-deal time at Thirty Madison and Remedy ended at the close of 2025. The company he had helped create would continue beyond his daily involvement. After years spent building it, he could step away and look back.
Looking back also meant discussing errors. His reflections have included acquisitions, rapid hiring and the difficulty of deciding when something is not working. Those subjects belong beside the financing and sale. They explain what occupied the years between the milestones, when the next decision came with incomplete information and the founders still had to make it.
“You get to that next phase, and you just realize you now have bigger problems to deal with.”
Demetri Karagas
Back with Steve, this time with Blake
Sentinel brings another longstanding irritation into the foreground: business certification. Its founders want a credential whose meaning remains clear after the initial review. Their proposed approach combines evidence, human review and continuing monitoring. The concern is familiar to anyone who has encountered a badge online and wondered what, precisely, it establishes.
Gutentag and Karagas are joined by Yoder, a former engineering director at Thirty Madison. Their stated ambition is to make a certification useful to companies, partners and consumers. It remains an early venture. At this stage, the revealing fact about Karagas is the choice itself: he has returned to a problem encountered while operating an earlier business, with people who shared that experience.
There is a pleasing continuity here. Sitesimon considered how people discover things online. Get Maid organised the steps between an online booking and work in an apartment. Thirty Madison required the founders to run brands and teams at a different scale. Sentinel asks what a company should have to demonstrate before others trust its credential. The products have changed; the interest in how an experience works persists.
His October announcement supplied the domestic interval between chapters: family travel, recharging and long lunches. That pause belongs in the story as much as any funding round. Karagas had time to stop. Then he chose colleagues, a problem and another beginning. Somewhere in New York, a lunch reservation may now require a little more planning.